Hydrocarbon distillate fuels



Unite 3,033,564 Patented May 8, 1 962 3,033,664 HYDRUCARBON DISTILLATE FUELS Samuel Richard Pethrick and David Tulloch McAllan, Sunbury-on-Thames, England, assignors to The British Petroleum Company Limited, London, England, a British joint-stock corporation No Drawing. Filed Dec. 22, 1958, Ser. No. 781,349 Claims priority, application Great Britain Dec. 24, 1957 16 Claims. (Cl. 44-53) icing troubles by the addition to the; gasoline of various additives. In particular, isopropanol and heXylene glycol have been found to be satisfactory anti-icing additives but, unfortunately, for them to be effective, these additives have to be added in amounts that are often uneconomical and, furthermore, since they are Water-soluble, they tend to be removed if the fuel is broughtinto contact with water which is often present in storage tanks or ms.

A gasoline composition has now been developed in which, to a large extent, the above disadvantages have been overcome.

According tothe invention, a motor gasoline at least 40%, particularly 45%, especially 50%, by volume of which distils over at 100 G, contains a small amount of an additive consisting of a substituted imidazoline having the formula I I (I) 1 ing a hydrocarbon chain having at least carbon atoms,

and X is hydrogen or a low molecular weight hydrocarbon or oxygenated hydrocarbon radical.

The additives may of course consist of a mixture of molecules of Formula I in which R and X have different values. Advantageously, R may be the hydrocarbon residue of a fatty acid RCOOH having 11-25 carbon atoms, most suitably the residue of oleic .acid, stearic acid or coconut fatty acids (the fatty acids obtained from coconut oil). Preferably X is an oxygenated hydrocarbon radical having not more than five carbon atoms, especially -CH CH OH.

According to a modification of the invention, the gasoline may contain instead of or in addition to a compound of Formula I, a small amount of a monocarboxylic fatty acid salt of such a compound, e.g. an oleic acid, stearic acid or coconut fatty acid salt of such a compound. Compounds of Formula I when combined with fatty acids are effective corrosion inhibitors in fuels.

The total amount of the additive should, in any case,

preferably be from 0.0005 to 0.05% by volume, especially The additives are compatible with other conventional gasoline additives such as anti-knock agents, anti-oxidants, upper cylinder lubricants or ignition control additives.

A number of tests were carried out to determine the icing times of a gasoline, and the same gasoline containing various anti-icing additives as indicated. The gasoline was a typical UK. premium grade motor gasoline estates Patent @fice where R is the hydrocarbon residue of a fatty acid (54% vol. distilled over at C.). The air supply to the engine was drawn through an ice tower approximately 6' high by 1' diameter and the icing time is defined as the time taken for the engine speed to fall from an initial 2700 rpm. to 2000 rpm. 7

The additives used were as follows:

A. Isopropanol.

B. Hexylene glycol.

C. 1(2-hydroxyethyl)-2-oleylimidazolinee2, i.e. a com.-

pound of Formula I in which R is the hydrocarbon residue of oleic acid, i.e.

and X is -CH CH OH.

D. The oleic acid salt of C. (This was prepared by mixing additive C with an equal amount of oleic acid.) The results of the tests are given in the following table.

The icing time given was, in each case, the mean of three runs.

Table Additive Percent Icing time Volume (minutes) A gasoline composition having an icing time of more than 60 minutes in the above test is known to give very satisfactory results in commercial use and it will be seen that the compositions according to the invention (the compositions containing additives C and D) were extremely satisfactory even when they contained only minute amounts of additive.

To determine the effect of water on the gasoline compositions according to the invention, the following test was carried out. A sample of motor gasoline containing 0.0025% additive C was agitated for a quarter of an hour in a metal drum with 5% by volume of water. The drum was then allowed to stand for 72 hours after which a portion of the gasoline layer was drawn oif. Its icing time was determined in the same manner as before and it was found to be still greater than 60 minutes. This evidence indicates that the fuel compositions according to the invention would not suffer a substantial reduction in their effectiveness during commercial storage in metal drums in thepresence of water.

We claim:

l. A motor gasoline, at least 40% by volume of which distills'over at 100 C., containing from 0.00050.05%

RCOOH having 11-25 carbon atoms and X is a hydroxyl-substituted hydrocarbon radical having 1-5 carbon atoms.

2. A motor gasoline according to claim 1, of which at least 45% by volume distils over at 100 C.

3. A motor gasoline according to claim 1, in which the fatty acid is amonocarhoxylic fatty acid selected from the, group. of monocarboxylic. fatty acids. consisting. of. oleic acid, stearic acid and coconut fatty acids.

4. A motor gasoline according to claim 1, in which the hydroxylrsubstituted hydrocarbon radical is 5.. A, motor gasoline. according. to claim 1? in which the substituted imidazoline is 1-(Z-hydroxyethylJ-Z-ole- 1yimidazo1ine-2.

6. A motor gasoline according to claim 1, in which the amount of the additive is 0.00050.02% by volume.

7. A motor gasoline according to claim 2, of which at least- 50% by volume distils over at 100 C.

8. A motorgasoline according to claim 5, in which the amount of the additive is :0005-0.0025% by volume.

9. A motor gasoline, at least 40%. byvolume of which distils over at 100 C., containing from 0.00050.05 by volume of an additive consisting of, a' salt of a monocarboxylic fatty :acid' selected'from the group of monocarboxylic :fatty acids consisting of oleic acid, stearic acidand coconut: fatty acids, with a substituted imidazo line having the, formula where R is the hydrocarbon residue of a fatty acid RCOOI-I having,1125 carbon atoms and X is a hydroxylsubstituted hydrocarbon radical having 1-5 carbon atoms.

10. A motor gasoline according to claim 9, of which atleast. by volume distilsover. at 100 C.

11. A motor gasoline according to claim 10, of which at least byvolume distils over at C.

12. A motor gasoline according to claim 9, in which the fatty acid is a monocarboxylic fatty acid selected from the group of monocarboXy-lic fatty acids consisting.

of oleic acid, stearic acid and coconut fatty acids.

13. A motor gasoline according to claim 9, in which the radical X is CH CH OH.

14. A motor gasoline according to claim 9 inwhich the substituted imidazoline is 1-(2-hydroxyethyl)-2-oleylimidazoline-Z.

15. A motor gasoline according to claim 9, in which the amount of the additive is 0.0005.0.02% by volume.

16.. A motor. gasoline. according to. claim 14, in which the amount of the additive is 0.00050.0025% by. volume;

' References Cited in the file of this patent Kobe, Elsevier Pub. (30., 1956, page 480. 

1. A MOTOR GASOLINE, AT LEAST 40% BY VOLUME OF WHICH DISTILLS OVER AT 100*C., CONTAINING FROM 0.0005-0.05% BY VOLUME OF AN ADDITIVE CONSISTING OF A SUBSTITUTED IMIDAZOLINE HAVING THE FORMULA 